Dec 9, 2024; Dallas, TX, USA; Boston Red Sox chief baseball officer Craig Breslow speaks with the media at the Hilton Anatole during the 2024 MLB Winter Meetings. Mandatory Credit: Jerome Miron-Imagn Images Jerome Miron-Imagn Images

Why Red Sox Haven't Struck In Free Agency Yet

Originally posted on Boston Red Sox on SI
By Patrick McAvoy | Last updated Dec 23, 2025 1:14 PM ET

The Boston Red Sox haven't struck in free agency yet, but that doesn't mean it hasn't been a successful offseason so far.

Boston entered the offseason with two significant needs: high-end starting pitching, at least one or two sluggers to add to the middle of the lineup. On Dec. 23, the Red Sox already have solved most of the team's needs, at least on paper. Sonny Gray and Johan Oviedo should give the Red Sox enough to maintain one of the better starting rotations in the American League.

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Willson Contreras is a very solid pickup and he didn't cost too much on the trade block. The Red Sox gave up Hunter Dobbins -- who was good in 2025 as a rookie but likely would've been a depth option for the team in 2026 -- plus two prospects. There is still plenty of time until Spring Training gets here and the club has made progress. If the team can strike in free agency -- either with Alex Bregman or someone like Bo Bichette -- then the offseason in general could be looked at as a major win.

The Red Sox still have plenty of room for more

On Monday night, Red Sox chief baseball officer Craig Breslow addressed the club's lack of free agent pickups and noted the team just hasn't "lined up yet," as transcribed by MassLive.com's Chris Cotillo.

"It’s not a deliberate or intentional decision to close off one pathway in favor of another," Breslow said, as transcribed by Cotillo. "We haven’t signed a free agent yet. That’s not because there aren’t free agents that we’ve been engaged in or because there aren’t really desirable targets in the free agent markets. We just haven’t lined up yet."

The "haven't lined up yet" part is interesting. It should be a comment that gives Red Sox fans a bit of hope because it's a sign that the club is still looking around and talking to people, but the longer they wait, the more likely the team could lose out.

The Major League Baseball offseason is long and very reactive among fanbases. Just because the Red Sox haven't signed a free agent yet, doesn't mean they won't. Boston has done a good job adding talent without having to hand out a nine-figure deal on the open market.

Boston still has flexibility. But it's not as if these moves didn't come with no cost. Gray's luxury tax number is $21 million for the 2026 season and Contreras' is $17.25 million, per Spotrac. The Red Sox have plenty of room for more and fortunately there are options and time for the organization.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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